Boston is a city that works hard, plays hard and moves fast. However, sometimes you need to hit pause and get away. Fortunately, one of the best things about living in or visiting Boston is how many amazing weekend trips are hours away by car, train or ferry.
Travelers have some pretty great options nearby that could satisfy their wanderlust. Whether you’re craving coastal charm, small-town quiet, mountain air or a food scene that rivals the city, there’s no shortage of places to recharge beyond Boston’s borders. This guide breaks down some of the best weekend getaways from Boston. Pack a weekender bag and let your energy reset near this cultural hub.
What Island Is Two Hours From Boston?
This island off the coast of Cape Cod is a bit over two hours from Boston when you combine car and ferry. You also can book a direct ferry in peak season from the city. It is located in Massachusetts and has become popular for north easterners trying to get away from the hustle and bustle of the city. Known for its beaches, bike paths, lighthouses, and laid-back luxury, Martha’s Vineyard is the spot for a summer weekend getaway.
Black-owned businesses, art galleries and cultural events thrive in towns like Oak Bluffs, which has deep roots in African American vacation culture. Travelers can make Martha’s Vineyard their next big day trip from Boston quite seamlessly since it is a popular tourist destination. However, a weekend trip is ideal, since there is so much to do and see there.
White Mountains, New Hampshire For Scenic Nature Escapes
Need mountains, lakes or hiking trails instead of city streets? This destination is under three hours from Boston and offers a quieter, greener pace. From hiking trails and scenic drives to ski resorts and waterfalls, the White Mountains are a top pick year-round. Towns, like Lincoln and North Conway, serve as great bases with easy access to Mount Washington and the Kancamagus Highway.
Nature lovers will appreciate the dramatic landscapes, abundant outdoor recreation opportunities and famous fall foliage here. This region is truly a great place to visit year round. There are many seasonal activities to get into. For example, visitors can go snowboarding in the winter and then fishing in the warmer months. These types of outdoor experiences are very popular and often keep visitors busy during their trip.
Visit A Coastal Town With Culture: Newport, Rhode Island
If you want sea breezes and good eats, this town, which is nearly two hours away by car, brings charm without the chaos. It is famous for its Gilded Age mansions, cliffside walks and seafood. Newport is also home to music festivals and a growing number of Black-owned and women-owned shops. It’s an elegant, but laid-back weekend option with vibrant waterfront views and a much different vibe from Boston.
For travelers who want to try something a bit different, Newport is great for one of many weekend trips from Boston. There are many opportunities to enjoy shopping, dining and sailing in Newport, so it is popular for both day trips and weekend escapes. Plus, there is an impressive maritime history to learn about and engage in. Getting out on the water and sailing yourself or checking out the yachts in the harbor on a relaxing walk are ideal. For a touch of Gilded Age opulence, there are also many mansions to tour.
Unique And Unexpected Getaways In Massachusetts
The first option in Massachusetts is Northampton, which is under a two-hour journey from Boston. This location is liberal and popular for being LGBTQ+ friendly. The town is full of bookstores, coffee shops and vintage finds. This college town in the Pioneer Valley makes a great escape for artists, introverts and weekend wanderers.
The downtown area has a reputation for being lively and overflowing with creative energy. It is ideal for travelers who want to explore a local and creative culture. There are a plethora of galleries, museums and theaters in the area.
Check Out Great Barrington, Massachusetts
Great Barrington is a Berkshire County gem that’s both sophisticated and grounded. Travelers can visit the W.E.B. Du Bois homesite, browse Black-owned boutiques and enjoy the farm-to-table food scene. Aside from that, this Massachusetts town is roaring with a unique small town charm. It is only a bit over two hours away by car, so it is a great option for weekend trips from Boston.
It has a striking natural beauty and vibrant local culture. In the downtown area, there are many shops and restaurants to explore. There is also a historic atmosphere, which adds a distinct cultural mark to any visitor’s experience. Overall though, the Berkshires are known for their serene and peaceful atmosphere, so this is a great and underrated place to visit.
Restful Retreats And Cultural Roots Around Boston
Not every weekend trip has to be about sightseeing. Sometimes, you just want peace. A space to unplug, reflect and reconnect with yourself, your people or nature. These spots offer slower rhythms and deeper grounding. Beyond the Berkshires lies the Western Massachusetts’ Hilltowns, a stretch of small towns— Ashfield, Chesterfield and Williamsburg— that feel like stepping into another timeline. There’s no traffic and no chain stores in these small towns, so a two-hour drive time is all that stands between Boston and these tranquil destinations. There are just winding roads, artists’ studios, river trails and woodstove-warmed inns.
Coastal Beauty In Old Lyme, Connecticut
Old Lyme is a lesser-known but beautifully preserved town on the Connecticut River. It is full of historical Black and Indigenous roots. And visitors can stay at a local inn, walk the marsh trails and explore community art at the Florence Griswold Museum. It’s calm, coastal and close enough to Boston for a 2-night recharge. For travelers trying to plan a trip, expect a two hour drive from the city to get there. And once you settle in, there is lots of coastal beauty to take in on the shoreline. This location is a cozy cultural hub with quaint shops and restaurants, which is perfect for an art focused getaway.
Tips For Planning A Relaxing Weekend Trip From Boston
If you want to go even deeper into self care on a trip from Boston, then there are several wellness and retreat centers within 90 minutes of the city. Places, like the Insight Meditation Society in Barre or the Kripalu Center in Stockbridge, offer weekend programming focused on healing, rest, and mindful movement. Even if structured retreats aren’t your thing, nearby farms and eco-lodges offer digital detox packages where you can swap your screen for stars, fresh air, and intentional silence.
These aren’t your typical tourist destinations, but they remind you that rest is revolutionary. For Black travelers who don’t always see themselves centered in the wellness space, these quiet corners create space to just be. Whether you need nature, culture, healing, or just a change of pace, Boston’s location gives you options. You don’t need to hop a flight to reset. Sometimes, clarity is just a couple hours up the road.
Frequently Asked Questions
How many days should be spent in Boston?
If a trip to Boston is also on the itinerary, then three days is ideal to explore without rushing. You can see major neighborhoods, like Back Bay, South End and the North End. Then, you can hit museums and historical sites and still have time for a day trip or harbor cruise then go on a weekend trip nearby.
What is the best month to visit Boston?
May through October offers the best weather and most events while traveling around Boston. September is especially beautiful. There’s warm days, cool nights and fewer crowds. Fall foliage begins to show by early October, making it a great time to explore both the city and nearby towns.
Where to stay in Boston without a car?
If you’re traveling without a car, then stay in Downtown, Back Bay, or near South Station. These areas are walkable, close to public transit, and offer easy access to Amtrak, commuter rail and buses for day trips. Hotels, like The Godfrey, The Verb, and even Airbnbs in the South End are great car-free options. To get around to nearby areas, the MBTA’s public transit system (“The T”) offers some public transportation options. There are subway, bus, trolley and ferry services available for travelers planning weekend trips from Boston.
